Option 1, he thought he was some cassanova and that she'd be impressed by the effort he put into stalking her. Women who fall for this... exist, but not without significant childhood trauma. The relationships (two) I've seen form under such conditions have been passionate, short-lived, abusive, and eventually involve the police.

Option 2, he has a humiliation/degradation kink and got exactly what he wanted.

Folk like that always see themselves the hero.

Getting a date and maybe more later?